HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 15907678, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | PyBOP | HCID 2724699 | — |
| Reactant | (S)-2-[3-(2-Benzyloxy-1-methylethyl)-2-(3,5-dimethyl-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoic acid | HCID 15887219 | — |
| Reactant | 7-Azabicyclo[2.2.1]heptane hydrochloride | HCID 16279503 | — |
| Reactant | Sodium chloride dihydrate | HCID 23713072 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 15907678 | HCID 15907678 | 94.4% |
Reaction Steps
PyBOP (1.51 g, 2.89 mmol) was added to a stirred mixture of the crude (S)-2-[3-(2-benzyloxy-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoic acid (1.20 g, 2.63 mmol), 7-azabicyclo[2.2.1]heptane hydrochloride (0.70 g, 5.26 mmol) and triethylamine (1.47 mL, 10.5 mmol) in dichloromethane (26 mL) at ambient temperature. After approximately 12 h, the reaction mixture was poured into water/brine (1:1) and extracted with ethyl acetate (×3). The combined organic extract was washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (gradient eluton; 60-75% ethyl acetate/hexanes as eluent) to give the title compound as a colourless foam (1.33 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06110931 |
| Source dataset | uspto-grants-2000_08 |
| ORD ID | ord-10fe1084a0f746f08e870263e5a25f13 |
| Source note | uspto-grants-2000_08 |